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Through her inspired juxtaposition of archival footage, home movies, and engaging interviews with five 30-something Muscovites born under Communism but who came of age around the collapse of the Soviet Union, director Robin Hessman’s engaging “My Perestroika’’ offers a surprising and revealing look at Russia’s past and present.

Anchoring the documentary are five former elementary school classmates whose insightful commentary illuminates Hessman’s mix of Soviet propaganda footage and more intimate home movies. Olga, a single mother, drives all over Moscow servicing billiard tables (“I’m called a manager. But that’s what everyone is called these days,’’ she notes wryly). Andrei has fared better under capitalism; his chain of stores sells pricey men’s dress shirts. A married couple who are teachers, Borya and Lyuba, talk about their journey from idealistic youth to a more resigned middle-age in the cramped but homey apartment they share with their young son, Mark. Their good friend Ruslan is a musician who used to be in a popular punk band. Now a father, too, he reminisces with Borya over vodka about the pleasure of reading “The Three Musketeers’’ during a childhood marked by “a real hunger for information.’’ Against shots of Pizza Huts and Mark plugged into his iPod, the fathers’ nostalgia for their youth during the Cold War is as poignant as it is humorous.

A graduate of Brown University, Hessman completed a five-year directing program in Moscow and was a producer for the Russian “Sesame Street.’’ Her familiarity with her subjects and the obvious time she spent with them pays off in remarkably intimate interviews and finely observed details of her subjects’ day-to-day lives.

There’s an absurdist quality to Hessman’s adroit visuals. Beautifully edited by Alla Kovgan and Garret Savage, the film mixes fascinating Soviet footage with family-shot films from the ’70s and ’80s. We get clips of “Swan Lake’’ as Ruslan notes that during times of national crisis, Soviet television broadcast the classic ballet in an endless loop. The 1991 dissolution of the Soviet Union, with its historic political, economic, and social upheaval, meant, as one subject says ruefully, that Russians were now able to buy jeans and chewing gum.

As they reminisce about the past, fret about the future, complain about the economy and political leadership (or lack of it), these ordinary Russians seem remarkably similar to many Americans in the 21st century. “My Perestroika’’ is a lively glimpse behind the Iron Curtain and a revealing look at us, too.

A special screening with filmmaker Robin Hessman in attendance is scheduled for Sunday at 3 p.m.